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Saturday was quite a special day, both for my wife/keyholder/mistress and for me. Her birthday was that weekend, and she decided that I would receive birthday spankings on her behalf. Rather than use her age, she set a high goal for me to earn release from chastity and an orgasm: 500 spanks.

With her help we made a little progress towards that during the week: 15. Only 485 spankings to go.

On Saturday we attended a play party with friends. This was a kinky party at a friend’s house in their BDSM dungeon. About 30 people attended. I picked up a Byerly’s birthday cake that was decorated with roses. I asked them to customize the frosting with her name, and to add thorns to the rose stems, which they did.

After we arrived at the party, my wife suggested that I let people know about my predicament. Most folks I asked were happy to help out by spanking my ass. So with my pants at my ankles and my CB-3000 visible, I received scores of birthday spankings. Most used a nice leather paddle that my wife prefers (similar to this but red). However, a few used their bare hands. Before very long I had over 300 and was pretty sore and pink.

Soon a special friend arrived at the party. I had phoned R earlier and asked her to participate in a special scene that my wife had wished for. A short while later the three of us were on the dungeon floor, where R and I stripped and laid down next to each other. My wife put on gloves and proceeded to fist us both at the same time. I was still locked in chastity, but during this scene R had three orgasms. My wife/mistress loved having one hand inside R’s pussy and the other inside my ass.

After that scene we cleaned up and then mingled with our friends some more. I asked for additional spankings. My wife said I had to stop at 480 so she could take over. I suspected she might quit at 499 and leave me locked up for the night. Indeed, at that point she administered the next 19 herself and stopped. I begged and pleaded for one more. To my surprise, she layed into my red rear with one more hard one, bringing my total to 500.

I asked to be unlocked, and she instructed me to retrieve the key from her keyring and ask someone else to unlock me. As it turns out, the couple who introduced my wife and I to each other were at the party, and I asked him to unlock me. He was happy to, as I suspected he might be, since he is also locked up at times. He knew what it meant for me to get unlocked.

Back in the dungeon, my wife had me strip again and lay in a leather sex sling with my legs up (like this but without the ropes). Apparently my orgasm would be here in front of everyone watching. She whispered something to R, who disappeared for a short while. My wife produced our largest dildo (similar to this), ready with a condom and lube. She held it at her waist and started fucking my ass with it. Due to it’s size, this is a very intense experience for me.

R returned and my wife asked her to masturbate me at the same time. A minute later my wife told me to close my eyes, turn my head, and open my mouth. I did so, and someone shoved their cock down my throat. He grabbed my hair and proceeded to fuck my face. I can’t do justice to how amazing this was – to be simultaneously used at both ends and jerked off. With so many sensations going it, it took me a few minutes to focus on the orgasm that was building. But before long I came and came and came. Having been locked up for a week, it was a wonderful orgasm, and the additional penetrations made it even more intense and incredible.

I opened my eyes and recognized D, a substantial presence in the local scene, as he took his cock out of my mouth. We both laughed, since I had sort of owed him this for a while. About a year ago I was crossdressed at another party here. Sitting in his lap, I got him all turned on but then had to run to a scene when my mistress called. Since then he had teased me about “finishing the job”.

Of course I’m locked back up now. My wife has been very appreciative of the dual fisting scene I helped arrange for her. And I’ve been so grateful to her, not only to have had an orgasm, but to have realized such an incredible fantasy with her. We are both aware of how fortunate we are to be together.

She finally broke me. As I wrote in my Violation and Transpotential posts, my wife/keyholder was not going to let me have another orgasm until I sang a song that I did not want to sing. She was willing to keep me locked up for 5 weeks before allowing me a release without singing it.

I gave in on Sunday. Coming to bed that evening she sexually teased me for a while, stimulating my nipples which makes me so horny. But the CB-3000 locked on me keeps my cock under 3.5 inches, pointed down, and small. It’s torture for me, and she enjoys it a lot. This went on for about 20 minutes, which can seem like hours to me as I writhe and desperately crave some genital stimulation.

She stopped and said she wanted Tiny (her name for my cock) and his house (the chastity cage) between her legs. I moved into position, essentially missionary, and gently pressed the cage against her pussy. She started grinding herself against it, and directed me about how much pressure she wanted. It was indescribably difficult to have my cock so close to her opening and feel nothing. She, on the other hand, was easily working herself towards a substantial orgasm.

I was aware of my cock pressing very hard against the inside of the solid plastic enclosure. It felt like the cage might burst open from the pressure, but it didn’t give, and my pulsing cock and balls ached so very much with each throb. I watched her slowly reach her climax. I felt genuinely and deeply honored to be providing her that pleasure, yet I could barely stand the pain radiating from my own genitals.

We then cuddled as she relaxed and floated in the afterglow of her orgasm. After a while she took my head and thrust my face into her armpit. I was surprised, but she smelled really good. Not perfume, but a natural scent of her own that pushed my arousal level through the roof. It was more than I could bear. I could not stand the sexual intensity for even one more minute. I caved in, and said that I would sing the song if I could please, please, please be allowed to orgasm.

She stopped, and was a little surprised. “Really? You’ll sing the song?” I consented, and begged to be allowed to orgasm inside her. She asked why. “It would feel so incredibly good to feel you, your pussy feels so wonderful and it feels like it has been forever. Please may I cum inside you, please Mistress?” I had no self respect left at all, the only thing that mattered was doing what she wanted in order to earn myself some sexual relief.

“Very well,” she said, “get Tiny unlocked. And since it’s going inside me, wash that skanky thing.” I threw on my robe and hurried downstairs to retrieve the key from her keyring and unlock myself. After a quick washing of my genitals, I was back upstairs and in bed. I felt so sexually activated, so fully aware of the urgent need for her body next to my body. It was more than just needing to cum, I needed to touch her, hold her, smell her, and feel her next to me.

I gently and sensuously attacked her, attending respectfully to her breasts, her lips, her thighs, feeling her hair between my fingers, smelling her deeply. It felt very close to what some would call a peak experience. I slowly entered her and savored the feeling of her warmth and wetness wrapping around my cock, which was finally fully hard after a week of captivity. I took my time and honored both of us, drinking in the sensations everywhere on my body. Even so, it still only took me a few minutes to climax.

But it was glorious. It was incredible. It felt so beyond words. I laid there and held her, and thanked her, and felt so in love and appreciative. What an amazing woman, to bring me to such a thrilling experience. Time was irrelevant as we lay together.

After a while we talked a bit, and she made it clear that she wanted me locked right back up in the morning. I agreed. It seems likely it will be at least another week of lockup for me. Saturday we have a play party, and she is really looking forward to it. It’s her birthday weekend, and guess who will be receiving her birthday spankings?

Last night my wife/keyholder allowed me out of the CB-6000 because she wanted to use me for her pleasure. However, by the time we finished watching a couple episodes of South Park, she was too tired. So I was able to sleep last night without my chastity device on for the first time in a week.

She woke up horny, and wasted no time in getting me hard and inside her. I took some time, letting her enjoy the sex we were having, and I focused on her. After a short while she had what seemed to be a very nice orgasm. I stayed inside her and we cuddled. I was hoping that I might be able to orgasm too — ideally without singing (see Violation).

Unfortunately some of our animals had an issue downstairs just then which required our attention. The moment was lost. Later she said I could have an orgasm, but I had to choose: either sing the song, or be locked up for another month. Damn! I nicely told her that I really didn’t want to sing the song, and she said that was fine, it was my choice, and that I should lock myself back up. Argh!

She said maybe she would give me another chance next week at the play party, where she might let me sing the song for our friends. I told her I wasn’t very likely to do that either. She said “Fine, it’s still your choice. I just know that it’s pushing a boundary for you, and I like to see you squirm about it. It just seems like a month is a long time, just because you don’t want to sing a little song.” I just agreed, dropped the subject, and locked Tiny (her name for my cock) back into his small plastic prison.

In my last post I said I’d write more about something we talked about a few days ago. I was locked up and she was sexually teasing me as she loves to do. We were also talking, and the conversation turned to crossdressing, which is something I like to do (I feel fortunate to be passable). She asked if I would like to be able to “live out”, meaning dress as a female all the time. I said that I would like that, and we discussed that in more detail.

Later in the conversation she asked me if I thought I was a man in a woman’s body, which I know is a basic issue with many transgendered people. I said no, but that I am extremely intrigued by the idea of actually being a woman physically. She spoke about having me castrated and how surgery could turn Tiny into a vagina. With some female hormones my body fat would redistribute, and I would grow some real breasts. Although I knew all this, I listened politely.

She asked me if I ever thought about that, and I truthfully answered “yes, more than once.” She asked me to rate how serious I would be about that, on a 0-10 scale. I thought about it, and said that it varied since sometimes I enjoy being male. My final answer was sometimes as low as 2, and sometimes as high as 7. I said I’d lived several decades as a man, and that I thought I would enjoy living some as a woman.

We discussed it some more, and I could tell she was really trying to get a sense for how I really felt about the issue. I don’t remember if I have mentioned here before, but her career has been in the medical profession. So if she wanted to figure out how to make it happen, I’m pretty sure she could accomplish it (legally). This conversation felt like an assessment of how likely I would be to provide consent for such a thing. I probably would not hesitate if she were sexually teasing me. That’s sort of frightening yet intriguing. Would my wife actually want to turn me into a woman?

She pointed out that we would still legally be married, even though we would both be biologically and legally female. That seemed pretty wild. She said that she would want to pick my new name, and I said that I would like that. One that came to her that we both liked was Mara.

Tonight we have tickets to a sold-out show, and we had talked about the possibility of me going crossdressed. I suspect it won’t happen for various reasons. Most likely I will start week 2 of being physically locked up. I note that, if this lasts a whole month, that will be 5 weeks without an orgasm for me. I really, really, really don’t want to sing that song, but can I last that long?

Just a quick post this morning. My wife/keyholder wanted oral two nights ago, and she ended up having two orgasms (me zero, of course). We also talked about something that I’ll write about at length next time.

I’ve been locked in the CB-6000 for a week now. I was thinking she might let me out soon. But this morning she said she’s thinking about leaving me locked up until a play party we’re going to next week. Another week! That would be my longest lockup yet. I know many other people have been locked up for longer, but for me two weeks without being able to touch my own cock will seem like a very long time.

My wife/keyholder extended my current chastity time by 3 days for a verbal outburst while driving. As I wrote in Extensions, she will delay my next orgasm when I get upset at other drivers when I’m driving and she is with me. Good thing I didn’t flip them off too — that would have cost me a total of 8 days!

Since I haven’t posted for a little while, I’ll take a moment to catch up.

Last weekend she decided she wanted access to my cock for her pleasure. She allowed me to penetrate her, and since I had been locked up for almost a week prior to that, it felt incredibly good! However, she controlled each step of our intercourse and kept it all about her desires. After a short while she had what appeared to be a really nice orgasm. I waited patiently, still inside her.

When she recovered, we chatted, and I started very slowly moving in and out of her again. She let me get away with it for a little while, then said that I wasn’t allowed to cum. It felt so amazingly wonderful that I begged and pleaded. She didn’t seem sure, so I kept asking and hoping, and eventually she said yes – with conditions.

She said I needed to tell her how many strokes I needed to orgasm, and I had to stop after that many whether I was done or not. I felt so close, so I said “ten”. Unfortunately, after 10 more strokes I wasn’t done! I stopped, and begged some more. She laughed, and I wasn’t sure what would happen next. After a bit more pleading she gave me one more chance. This time I said 25, she said ok, and after 22 I had an incredible orgasm. Wow.

Fast forward to the next evening. A few things happened, and I guess I was a little bit snippy (or so she said – one doesn’t argue with such things). Regardless, she made it clear that she wanted me locked back up right away. “I’m learning that you behave so much better when you’re locked up. It really is clear that you need to have that tiny cock under control to help you act properly at all times. And I think this next time period is going to be a long one.” Humph.

Since then I’ve only been briefly released for a couple’s massage we had yesterday. Otherwise it’s been 5 days of wearing the CB-3000. Quite a few of those days have included her merciless sexual teasing with no release.

A few days ago she gave me the opportunity to have an orgasm. “All” I had to do was sing a song. I refused. You are probably thinking that I’m nuts. Maybe I am. But I found her request to be strange and emotionally cruel, for me. You see, I don’t believe in a god. So what? Well, the song she wants me to sing is the child’s song “Jesus Loves Me”.

I’m sure all the Femdom’s will get a great chuckle out of that. There’s some odd principle aspect about it that I am having trouble with. Perhaps I can eventually see it as mere temporary humiliation. But right now I feel like I would be betraying myself in some way to go through with it. Of course she is having a great time with this.

One other item to share. I was out volunteering recently, and the public men’s bathroom there had these open-style wide urinals. I could have used a stall and sat down, of course. But took a chance and peed with my locked-in-plastic cock in my hand. No one else came in when I did it, but it was an awkward reminder of my chastity. There are times I wish my chastity device gave me no choice but to sit to pee. Perhaps a future device of mine will enforce that.